Although I've done plenty of racing with Dennis Conner over the years, it had been nearly 25 years since I'd gone offshore in a race with him. It was during an SORC in the early 80s when I got to do my first race with Mr. America's Cup. Back then Dennis was still approaching the height of his America's Cup accomplishments. He'd already won the Cup twice, but his biggest victory, in Fremantle, was yet to come. I remember being amazed by his mathematical mind, how he could take a few tidbits from our navigator—the legendary E. Ben Mitchell—and convert them into tactical axioms that became the crux of our game plan.

It didn't take long for those memories to be rekindled as we headed out of San Diego harbor on Dennis's Farr 60 Stars & Stripes enroute to Puerto Vallarta, Mexico, 1000 miles down the coast. I was doing the navigating and we had barely cleared the harbor before DC began peppering me with questions relating to the racetrack and the weather forecast. Whereas most offshore sailors today use computers and weather GRIB files to help determine strategy, Dennis still does it all (or mostly all) in his head. He's a master at calculating the geometrics of VMC (velocity made good on course) so important in sail selection and steering, and he's done so many Mexico races that he knows the coastline and the local conditions better than most. For the next four and a half days, whilst I mined the tactical information available on the boat's computer, DC kept up his mental navigation calculations going as a check to the computer numbers.

Every morning at 0830, the fleet roll call was conducted. As I typed away the positions of the fleet into Expedition, I quickly reported to DC the range and bearing of our top competitors. By the time I'd finished entering the positions and letting Expedition crunch the numbers to determine the handicap positions of the fleet, Dennis had already figured out the time deltas of most of the competition.

The current Stars & Stripes is the biggest offshore racing boat that DC has owned and his goal with the boat is to enjoy some good "local" racing with his friends. For this race we had a varied crew ranging from DC's father-in-law, John Bell, sailing in his first Mexico race, to 14-year-old Jake Ladow, another race newby and grandson to DC's long-time friend, Jerry Ladow, a veteran of over fifty years of Mexican races, and the primary chef for our race to Puerto Vallarta. To keep the Ladow generation line intact, Jake's father, Andy was also aboard adding his skills to the driving and trimming team.

Speaking of food, that was certainly a highlight of our race. DC promised great meals all the way down the coast and he didn't let us down. No freeze-dried for us. Dinners were gourmet affairs that included grilled swordfish on the stern-mounted hibachi, steak, shrimp, and lobster. The homemade brownies only lasted through the first three nights—there's nothing like a good brownie at 3 a.m.—but there were still plenty of munchies for the 15-mile motor from the finish line to the harbor.

How'd we do? Well, as the wind swung aft and our closest competition, two Santa Cruz 70 sleds, started to sail away from us on the second day, we realized that it was going to be a tough race, because Mexican races are predominately downwind. But we sailed hard and were happy with a second-place finish in Class 2. The faster Class 1 boats got into Puerto Vallarta before the high pressure started to kill the wind in the Sea of Cortez—our final 24 hours featured some classic slatting conditions—and Doug Baker's Magnitude 80 shredded the course to set a new record. But there were no complaints from the crew of Stars & Stripes, DC kept us well fed, focused on our performance, and we were sailing downwind in some of the most beautiful waters in the world.

For results, photo galleries and more on the San Diego YC's Puerto Vallarta Race, click here.